Holiday houses in Milwaukee County

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Top-rated holiday rentals in Milwaukee County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
A bright living area showcases a comfortable seating arrangement with decorative cushions. Potted plants add greenery, and light streams in through the large windows. Artwork adorns the walls, while a mix of textures is provided by the rugs and furnishings.
Apartment in Milwaukee
4.94 out of 5 average rating, 442 reviews

Bay View MKE Hideaway - with Parking!

Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

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Guest favourite
A spacious back yard overlooks Lake Michigan, featuring a manicured lawn and five comfortable seating options. Sailboats are visible on the water, with a breakwater in the distance. The serene setting is framed by lush greenery, inviting relaxation and enjoyment of the scenic view.
Apartment in Milwaukee
4.86 out of 5 average rating, 316 reviews

Lakeside Beauty

Stunning lower duplex on Lake Michigan in beautiful Bay View WI. Exceptionally large 2 bedroom unit boasts back yard overlooking Lake Michigan with fire pit for cozy evening fires. Unit is a mix of new and classic vintage. Walking distance to South Shore Yacht Club, South Shore Terrace Beer Garden, Award Winning restaurants, a unique European grocery store, and the second largest Farmer's Market in the state. Seven minutes to downtown Milwaukee. Owner lives upstairs. Two bikes available.

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Top Guest favourite
A charming upper unit of a bungalow is surrounded by lush green trees and well-maintained landscaping. The exterior features a combination of brick and stone, with decorative patriotic bunting adorning the porch. A pathway leads to the entrance, framed by vibrant foliage.
Apartment in Milwaukee
4.93 out of 5 average rating, 105 reviews

Charming Bungalow Unit Just North of Downtown Milw

Here’s an opportunity that can’t be beat! This fully furnished upper unit in a charming bungalow is ready to be your home base while in Milwaukee. Two bedrooms, one fitted with a king size bed and one with a queen. Full kitchen. Plenty of street parking in this walk able niche neighborhood. Near Downtown, UW-Milwaukee, MSOE, The Milwaukee RiverWalk as well as a quick hop, skip and jump to museums, tours and arenas/stadiums. Easy access to public transportation. No cleaning fees!

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Top Guest favourite
A stylish living room features a combination of modern and vintage decor. A leather sofa and two vibrant red chairs are arranged around a wooden coffee table. Decorative plants and unique light fixtures add character, while floral wallpaper and a colorful dining area can be seen in the background.
Home in Milwaukee
5 out of 5 average rating, 168 reviews

Fabulous Walkers Point Mansion w/ Bar andFireplace

This stunning Walker's Point historic mansion is completely re-imagined with interior spaces that will delight you and your guests. Host a memorable get together with friends or family and relax by the bioethanol fireplace, enjoy everything the vibrant neighborhood has to offer. We have some beautiful spaces for your enjoyment, including a finished-attic hangout space, and a secret vintage-inspired lounge in the basement. Enjoy plenty of Milwaukee history in a spectacular new form!

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Top Guest favourite
A comfortable sectional sofa adorned with colorful throw pillows is positioned around a low wooden coffee table. A projector is set up for viewing, with a light-colored rug adding warmth to the space. Artwork in vibrant hues is displayed on the walls.
Home in Milwaukee
4.93 out of 5 average rating, 160 reviews

Quiet Bay View Getaway

Enjoy this modern, updated 1 bedroom, 1 full bath, private lower suite located across from the airport and just minutes from Lake Michigan, downtown, and trendy Bayview nightlife! Conveniently located less than 2 minutes from multiple freeways! Walking distance to many restaurants and coffee shops. Less than a 9 minute drive to Miller Park, Fiserv Forum, State Fair, and more! Perfect for couples or traveling professionals who want easy access to everything Milwaukee has to offer!

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Top Guest favourite
Guest suite in South Milwaukee
4.99 out of 5 average rating, 100 reviews

Historic Hawthorne House

Nestled just steps from Grant Park Beach & Lake Michigan, the scenic Seven Bridges Trail, and the lush Grant Park Golf Course, this unique rental offers a blend of history, charm and comfort. Only a 10 minute drive to Mitchell International Airport and an easy 20 min drive to downtown Milwaukee. Whether you're here to unwind in nature, explore the local parks, enjoy a peaceful lakeside stay, or enjoy the best that Milwaukee has to offer this home has everything you need.

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Top Guest favourite
A well-equipped kitchen features white cabinetry, stainless steel appliances, and green tile backsplash. The space is illuminated with recessed lighting and includes a dining area with a wood table. An open doorway leads to another room, enhancing the overall flow of the layout.
Home in Shorewood
4.92 out of 5 average rating, 159 reviews

Shorewood house - near shops w/ WiFi & parking

Just down the road from Lake Michigan, this charming duplex upper is the perfect space for a relaxing getaway. After a day of shopping, eating good food, and exploring Milwaukee, look forward to kicking back in the cozy living room, or on the patio. This duplex has 2 bedrooms; a King bed master, and one bedroom with two Twins. There is one charming bathroom with a bathtub. Well stocked kitchen, and plenty of backyard space. The lower tenant is respectful of guests.

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Top Guest favourite
Home in Cudahy
5 out of 5 average rating, 57 reviews

Lake Michigan Views • Private Cedar Sauna

Private cedar barrel sauna, cozy fireplace, and peaceful outdoor spaces just steps from Lake Michigan. Unwind beneath the string lights in the seasonal Garden Lounge, gather around the chiminea, or stroll scenic bluff trails along the lake. Just minutes from downtown Milwaukee, beaches, breweries, restaurants, museums, festivals, and sporting events, this thoughtfully designed getaway is the perfect home base to relax, recharge, and explore year-round

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Guest favourite
Home in Milwaukee
4.92 out of 5 average rating, 38 reviews

NEW! Sunny Pet Friendly Upper Unit - Bay View

This sunny upstiars unit of a Bay View bungalow duplex is so sweet and cozy. It features 2 bedrooms, each with a queen bed and closet. The kitchen is stocked with dishes, utensils, pots and pans, microwave, gas range, refrigerator, toaster, and Keurig coffee maker. The bathroom has a shower/bathtub and hair dryer available. Laundry is in the basement and is available for guests to use. Street parking is available, but is not always free.

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Superhost
Apartment in Milwaukee
4.92 out of 5 average rating, 334 reviews

Modern Luxury 1BR Apt with Rooftop+Gym+Parking

Experience Milwaukee like a VIP! This luxury one-bedroom apartment offers the ultimate convenience with direct access to the Fiserv Forum through the building's enclosed skywalk. Whether you're in town for a game, a concert, or simply to explore, you'll love taking in the skyline views from the rooftop patio, working up a sweat in the fitness center, or relaxing in your sleek and comfortable private space.

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Top Guest favourite
A spacious living area features large windows providing views of Lake Michigan. A light wood dining table is paired with white chairs, and a cozy sectional sofa invites relaxation. Artistic pieces adorn the walls, enhancing the bright and airy atmosphere.
Apartment in Milwaukee
4.99 out of 5 average rating, 237 reviews

Lakeview Downtown Milwaukee Condo

This charming one bedroom offers a full kitchen, king bed, private full bathroom, dining and living room area. Conveniently located in Milwaukee's East Side - close proximity to lake paths and trails, Juneau park, Brady Street, Fiserv Forum, the Art Museum and Summerfest grounds! Stay here and start your day with a beautiful sunrise in one of the best locations Milwaukee has to offer.

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Guest favourite
A charming blue exterior is presented, featuring a white staircase leading to the entrance door. The porch is framed by a railing, and windows are positioned symmetrically on either side. Surrounding greenery adds a natural touch to the home's inviting appearance.
Apartment in Milwaukee
4.96 out of 5 average rating, 478 reviews

Bremen Street House | Lower Flat

Milwaukee is home to a distinctive architectural style known as "Polish flats," found predominantly in the Riverwest neighborhood. Just west of the Milwaukee River, this location is only blocks from the Oak Leaf bike trail, with an array of independent coffee shops, roasters, restaurants, bars, and breweries all within easy walking distance.

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Popular amenities for Milwaukee County holiday rentals

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